TW299319B - - Google Patents

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Info

Publication number: TW299319B
Authority: TW; Taiwan
Prior art keywords: acid; japan; methacrylic acid; weight; water
Prior art date: 1994-11-04

Application number

TW084111568A

Other languages

English (en)

Chinese (zh)

Original Assignee

Mitsui Toatsu Chemicals

Kurarey Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-11-04

Filing date

1995-11-02

Publication date

1997-03-01

1995-11-02 Application filed by Mitsui Toatsu Chemicals, Kurarey Co Ltd filed Critical Mitsui Toatsu Chemicals

1997-03-01 Application granted granted Critical

1997-03-01 Publication of TW299319B publication Critical patent/TW299319B/zh

Links

CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 62
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
239000007788 liquid Substances 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
238000011049 filling Methods 0.000 claims description 11
238000000605 extraction Methods 0.000 claims description 10
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 8
229910052750 molybdenum Inorganic materials 0.000 claims description 8
239000011733 molybdenum Substances 0.000 claims description 8
238000007670 refining Methods 0.000 claims description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
230000002079 cooperative effect Effects 0.000 claims description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000006555 catalytic reaction Methods 0.000 claims 1
239000013043 chemical agent Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
150000001993 dienes Chemical class 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000001294 propane Substances 0.000 claims 1
239000013589 supplement Substances 0.000 claims 1
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
239000000284 extract Substances 0.000 description 37
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 35
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 35
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 27
239000007864 aqueous solution Substances 0.000 description 27
239000011976 maleic acid Substances 0.000 description 27
239000012535 impurity Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 10
238000002309 gasification Methods 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
239000012071 phase Substances 0.000 description 10
238000010025 steaming Methods 0.000 description 10
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000007789 gas Substances 0.000 description 9
239000012495 reaction gas Substances 0.000 description 9
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000000710 polymer precipitation Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000002699 waste material Substances 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
241000270722 Crocodylidae Species 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000002131 composite material Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000011964 heteropoly acid Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
241000282346 Meles meles Species 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
-1 aromatic carboxylic acids Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW084111568A 1994-11-04 1995-11-02 TW299319B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6270826A JPH08134011A (ja)	1994-11-04	1994-11-04	メタクリル酸の精製方法

Publications (1)

Publication Number	Publication Date
TW299319B true TW299319B (fr)	1997-03-01

Family

ID=17491557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW084111568A TW299319B (fr)	1994-11-04	1995-11-02

Country Status (8)

Country	Link
US (1)	US5959142A (fr)
EP (1)	EP0710643B1 (fr)
JP (1)	JPH08134011A (fr)
KR (1)	KR100189509B1 (fr)
CN (1)	CN1068304C (fr)
DE (1)	DE69505335T2 (fr)
MY (1)	MY115630A (fr)
TW (1)	TW299319B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19709392A1 (de) *	1997-03-07	1998-09-10	Basf Ag	Verfahren zur Extraktion von (Meth)acrylsäure
CN1297454C (zh) *	2001-11-07	2007-01-31	三菱化学株式会社	贮存易于聚合的化合物的储罐及贮存的方法
DE10314203B4 (de) *	2003-03-28	2005-10-06	Stockhausen Gmbh	Verfahren zur Abtrennung von (Meth)Acrylsäure aus einer (Meth)Acrylsäure-haltigen Zusammensetzung
EP1879846B1 (fr) *	2005-04-27	2009-07-15	Basf Se	Procede de separation par rectification d'un liquide contenant de l'acide acrylique et/ou de l'acide methacrylique
EP2085376B1 (fr)	2008-01-30	2012-09-05	Evonik Röhm GmbH	Procédé pour la préparation d'acide méthacrylique de grande pureté
US9216938B2 (en)	2011-02-09	2015-12-22	Lucite International Uk Limited	Process for the production of (meth)acrylic acid and derivatives and polyers produced therefrom
WO2013163806A1 (fr)	2012-05-03	2013-11-07	Evonik Industries Ag	Procédé de préparation d'acide méthacrylique de haute pureté, qui ne jaunit pas
JP2016516732A (ja)	2013-03-18	2016-06-09	エボニックレームゲゼルシャフトミットベシュレンクテルハフツングＥｖｏｎｉｋＲｏｅｈｍＧｍｂＨ	メタクリル酸及びメタクリル酸エステルの製造方法
CN103819331B (zh) *	2014-02-28	2015-08-05	山东易达利化工有限公司	一种甲基丙烯酸的脱色和提纯方法
WO2017188220A1 (fr) *	2016-04-28	2017-11-02	三菱ケミカル株式会社	Procédé de purification et procédé de production d'acide méthacrylique
EP3608305A1 (fr)	2018-08-10	2020-02-12	Röhm GmbH	Procédé de production d'acide méthacrylique ou d'esters d'acide méthacrylique

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE862887C (de) *	1943-05-13	1953-01-15	Basf Ag	Verfahren zur Gewinnung wasserloeslicher organischer Saeuren
FR1084487A (fr) *	1953-09-30	1955-01-19	Anglo Iranian Oil Co Ltd	Procédé de séparation d'acides gras à partir de mélanges organiques
GB997325A (en) *	1963-06-20	1965-07-07	Distillers Co Yeast Ltd	Recovery of acrylic acid
JPS6016927B2 (ja) *	1979-07-19	1985-04-30	三菱レイヨン株式会社	メタクリル酸の抽出分離法
JPS60152438A (ja)	1984-01-21	1985-08-10	Nippon Shokubai Kagaku Kogyo Co Ltd	メタクリル酸の精製方法
JPH066551B2 (ja)	1984-02-24	1994-01-26	日本化薬株式会社	メタクリル酸の精製分離方法
US4879412A (en)	1985-03-14	1989-11-07	Mitsui Toatsu Chemicals, Inc.	Purification process of methacrylic acid
US5196578A (en)	1987-10-09	1993-03-23	Mitsui Toatsu Chemicals, Incorporated	Purification process of methacrylic acid
JPH01193740A (ja)	1988-01-29	1989-08-03	Konica Corp	熱現像画形成装置
DE3844087A1 (de) *	1988-12-28	1990-07-05	Basf Ag	Verfahren zur herstellung von methacrylsaeure durch oxidation von methacrolein

1994
- 1994-11-04 JP JP6270826A patent/JPH08134011A/ja active Pending
1995
- 1995-10-31 US US08/550,801 patent/US5959142A/en not_active Expired - Lifetime
- 1995-11-02 DE DE69505335T patent/DE69505335T2/de not_active Expired - Lifetime
- 1995-11-02 TW TW084111568A patent/TW299319B/zh not_active IP Right Cessation
- 1995-11-02 EP EP95307838A patent/EP0710643B1/fr not_active Expired - Lifetime
- 1995-11-02 MY MYPI95003321A patent/MY115630A/en unknown
- 1995-11-03 KR KR1019950039540A patent/KR100189509B1/ko not_active Expired - Lifetime
- 1995-11-04 CN CN95119027A patent/CN1068304C/zh not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CN1068304C (zh)	2001-07-11
JPH08134011A (ja)	1996-05-28
DE69505335D1 (de)	1998-11-19
KR100189509B1 (ko)	1999-06-01
MY115630A (en)	2003-08-30
CN1127746A (zh)	1996-07-31
KR960017613A (ko)	1996-06-17
US5959142A (en)	1999-09-28
DE69505335T2 (de)	1999-03-04
EP0710643A1 (fr)	1996-05-08
EP0710643B1 (fr)	1998-10-14

Legal Events

Date	Code	Title	Description
2015-12-11	MK4A	Expiration of patent term of an invention patent

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US5675055A (en)	1997-10-07	Acidification/extraction treatment of waste caustic stream
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